Work at a Trek shop. Lost my MTB trails...Which Madone?

So I work at a Trek shop and need to decide which road bike I plan to buy this week. I race my Superfly, but just graduated from a school with a massive MTB scene and am now in an area where all trails are over 1.5 hours away. So, I am picking up a road bike to train on with the local road crew and also race over the next few years.

Right now I am looking at the Madone 5.5 and Madone 5.2. I am also considering the Madone 6.5.

I live in an area in West Virginia with plenty of hills and I'll be honest folks, I know my mountain bikes but don't have the first clue about road bikes. Should I go with SRAM Force or Shimano Ultegra? Check out the links and give me your opinion if you can help out. Thanks!